I had been dating a guy for maybe a couple of months when we went on this date. We were still very young. One evening he called me up asking me if I knew his two friends. One I will name Matt, the other Sue. I happened to know Matt. He often made fun of me when we attended the same school. I told my boyfriend so and said I did not like him. Just so happens I was on speaker phone and Matt and Sue were there! Great. After that awkwardness, my boyfriend told me the three of them were going to see a movie, and asked if I wanted to go along with them. I agreed – I wanted very much to see him, since I didn’t get to very often.

So they rolled up to my house eventually and I got in the car. Someone’s parents were driving (as I said, fairly young still). I was surrounded by a bunch of people I didn’t really know and not exactly feeling confident about it. As we rolled along to the mall for the movie, a small child popped up out of the seat behind my boyfriend and I, trying to frighten me. Apparently, they were a younger sister of Matt or Sue. Everyone laughed and stared at me with smiles on their faces like it was supposed to be funny or something. I was less than amused since I was already feeling out of place. That didn’t help.

Then we reached the movie theater and got in line to buy tickets…at least, I did. My boyfriend informed me that he didn’t have money to pay for the movie, but they had connections so he was going to get in anyway. After some shady dealing at a water fountain and “secretive” hand brushing with their “connection,” we got into the movie without a problem. Well, without being caught anyway.

We were then sitting in the theater, watching the movie. The boyfriend decided it was time to kiss, and apparently pretty aggressively because I was being sunk into my seat in an awkward position. His friends moved a couple of seats away. Awkward. And on top of that, my boyfriend was hardly able to keep his eyes open because he was so tired.

It was all dreadfully awkward and even if I didn’t see how terrible it was when it was happening, I definitely see it now.

I had a couple more pretty bad dates with the kid, but eventually we broke up and I met an amazing boy that has been in my possession for a good couple of years.

I met M, a gorgeous Indian guy, at a tango dance. We hit it off, talking about dance (he also liked salsa) and our jobs, and exchanged numbers.

A couple of days later, he called while I was at happy hour in his neighborhood, so I agreed to meet up afterward. I told him I was done drinking but would happily share an appetizer, but he insisted on ordering a whole bottle of sparkling wine. The whole conversation consisted of him trying everything he could think of to alternately impress me and get me up to his apartment. My lack of interest in a second date was confirmed by a terrible kiss at my subway stop, and I spent the whole night sick from the glass of wine he’d pressured me into drinking on top of everything I’d had at happy hour.

But what makes the story is a conversation I had with a new boyfriend a few weeks later. He was telling me how he had been out salsa dancing in that neighborhood, and this Indian guy named M (an uncommon name) had been all over one of our mutual friends. We both cracked up when I said, “I went out with that guy!”

I met My Very Worst Date at a New Years Eve function at a somewhat swanky hotel. He was one of the bartenders and kept slipping me free drinks. I didn’t think it was a big deal because, hey, New Year’s Eve is my birthday, and really, who pays for drinks on their birthday?

Fast forward to a few weeks later: I got a phone call at work, through the switchboard. Weird, because the department I was in had a direct line, but, whatever. It was MVWD, asking me out. I accepted, thinking “cool!”

So, the night of the date, I was getting ready when he called to say that I needed to come get him because it was raining and all he has is a motorcycle. I thought this was a strange request but I was hungry and I was all dolled up. I got to his house (which is a filthy basement suite) and all he could blabber on about was his daughter “who is the light of his life” and how much I’d love being in his daughter’s life. Now I’m one of those childfree people and am EXTREMELY uncomfortable around babies and toddlers. So I hinted how hungry I was and “I’m gonna pass out if I don’t get some food in my stomach.” We went out to a dive-y hotel bar (which also has a casino upstairs). I ordered chicken strips and he started freaking out about the price. Whatever, I never asked him for gas money, he can pay for a $9 side of chicken strips and a $3 beer.

After dinner, he said “Let’s go to the casino!” I thought, well, okay, I’ve got twenty bucks and I’ll sink it into a penny slot. He disappeared. I was doing well on this penny machine – got up to around a hundred bucks, and he came slinking up to me, asking me if I had any money because he just spent his paycheck on roulette. Awesome. Then he said “I should have told you earlier. I’m a gambling addict.” I gave him two dollars and told him to bugger off.

I cashed out my hundred bucks and lit on out of there. I wasn’t wasting more gas driving him home, not after this miserable date! I lived about five minutes away, to drive him home was another 20 minutes. Screw that noise!

I never did hear from him again. However, the DJ at the New Year’s Eve party was the one who told him where I worked and called me to see how the date went. Awesome.

My Very Worst Date happened my sophomore year of high school. I had pushed the memory so far into the back of my mind that I forgot about it all these years until reading enough stories on this site for the pain and humiliation to all come flooding back.

I was in a long term relationship with my boyfriend-at-the-time M, who I had known for about 3 years (and dated 2 years), and he was riding buses all the way from California to come see me in Texas. It seemed almost perfect and unreal, as I thought we’d never see each other again. He was coming down for a few days on his two week Christmas break, and was going to stay at my house. Now, if you’re wondering how my mother felt about a 17-going-on-18 year old boy staying with her barely-turned 15 year old daughter, well she was DELIGHTED. My mom, being a heavy drinker and party go-er at the time, seemed more excited than I was, and was willing to take us out to a fancy dinner, and pay for our food (because he spent all his money on his bus tickets). I thought this was some kind of Christmas miracle. I wasn’t more wrong about something in my entire life.

The first night he came over my mom delayed our plans to day 2 because she was at some club somewhere too smashed to drive us anywhere, and wasn’t coming home. We were a bit nervous, seeing as he only had 3 days including the day he came and the day he would leave which was to be in the mid afternoon. So we stayed home, messed around, and had fun, and couldn’t wait for the next day.

The next night my mom called and told us to dress nicely as we were about to leave to dinner. I wore a tight, thinly-clothed dress shirt, with some skinny jeans (I didn’t have anything nicer), while he wore a Devil Wears Prada shirt with some baggy jeans (he didn’t bring anything nicer), but I really didn’t care how he dressed, and thought nothing of it. About 4 hours late, my mom arrived, and we were soon driven out of the city, and into the middle of nowhere at about 9 o’clock at night. We had been driving for about 45 minutes and already I was sweating in anticipation for what mysterious, horrible night could come of this. I was not prepared for what was to be my very worst date with my very best boyfriend.

We finally arrived at what looked to be an abandoned shack in the middle of an abandoned parking lot in the middle of nowhere. Loud music was playing from inside and there were drunk people waddling in and out of the bar. Before I could even ask or beg my mom to drive us back, she turned to us and smiled “Here we are! I know all of the bartenders here, and since no cops know about this place, you two can get wasted all you like! Just remember, if you want to get busy though, you’ll have to come ask me for my car keys ‘cause I don’t want no one watchin’ ya’ll inside.” I was amazed, and astounded by those words alone. She then proceeded to warn us about talking to the people inside because most of them were ex convicts, registered sex offenders, junkies, or drug dealers. M and I were drug and alcohol free, abstinent teens trapped in the middle of nowhere with a bar full of psychos- and my mom. Could it have possibly gotten any worse?

It was about 10 o’clock at night, and the weather outside was in the low twenties. We didn’t have our jackets, and we were too afraid to go inside the bar. The only light outside was a light hanging above the door that only lighted a small circle on the pavement where we sat, being startled by anyone coming in or out. I was crying and I’m pretty sure he was too, but it was hard to tell seeing as our tears froze to our cheeks. We decided freezing to death huddled under a light bulb wasn’t how we wanted it to end, so around 12 in morning we decided to take our equally dangerous chances inside.

The temperature change was enough to instantly kill someone or put them in shock. From below twenty and rapidly decreasing weather outside, we walked into an oven fueled by cigarette smoke alone. It was probably about 85-90 degrees in that shithole of a bar. To make matters worse, we found out why the music was so, so awful. It was karaoke night! We made our way to a secluded corner, and sat on some old, rickety bar stools. We tried to talk, but we couldn’t even understand what we were saying much less see each other through all the smoke. Never having smoked before, we were both coughing our lungs out, all while trying to push off drunk people who thought we were so “hip” and “young looking”.

After being hit on, and almost dragged into a few drunken fights, my mom swayed over, and can you believe it, her already slutty tank top’s straps had been cut off and her shirt was pulled over her stomach only covering her boobs which didn’t hide much because her bra was missing (did I mention my mom is like over 300 pounds?). She told us how happy she was we came inside to hear her sing next (my heart plummeted even lower) and she ran onto the stage and sang. When I say she sang I really mean she screamed, literally screamed, the lyrics to Santeria by Sublime. I give her credit for remembering the lyrics, but even M cracked a smile at her dreaded performance. We decided to take our chances outside. Again. Because she was that bad, and I was about to strangle myself just to get out of this nightmare quicker.

It was about 2 am, and I prayed that if God had mercy on our souls, he would send someone down to rescue us. M knew I was humiliated, and tried to cheer me up by showing me some of the cool, underground music he listened to in CA. After a few songs, my body had become completely numb, and the cold was no longer a problem to the both of us. Just as I began to drift off leaning on his shoulder we were both shoved face first into the pavement- breaking his brand new video ipod and headphones completely. What happened? Two drunk bitches who had both been proposed too (I wonder who the lucky guys were) had been too drunk to walk and had fallen over us. An apology? Even a “F*** you” would have been great. No.. for the next hour and a half, these two women went on and told us their fabulous stories of their fiancées and how they cheat on them every so often and how one of them had just had sex with some junkie in the bathroom. When their rides FINALLY came, one of them wanted to show M their ring one last time – and punched him right in the nose by accident. They were helped by some guys who laughed at us and mocked us. I held M’s shattered-screened ipod, and he wiped his bloody nose on his shirt (which I later found out was also new). We went back inside.

We sat in misery in the corner again. No one even asked him why he had blood all over his face and shirt, or why I was sitting their shaking like a mad person. Finally, after sitting around for 2 hours (yes, it was past 5 IN THE FREAKING MORNING) I found my mom, and this is where my real story starts. She could barely stand and had been using the crowd of people as means of standing up. She FELL onto my boyfriend’s lap. She was able to drag herself up, and I cannot describe to you the horror on his face nor mine when she started KISSING HIS NECK. He shoved her away, but (did I mention she was like over 300 pounds?) she was too big for him and just kept pushing on. As soon as I grabbed her she stood up and lifted her shirt exposing her boobs. She leaned on him again and asked him if he’d like to take a visit to the restroom with her. I screamed at the top of my lungs, which startled her and caused her to fall backwards. Me and M got the hell out of there!!

Back outside I was raving and ranting about how pissed I was, and how she was my own mother and hit on my boyfriend and what-not. M actually thought it was kind of funny, and still tried to cheer me up. We did manage to have a little bit of fun by kicking an empty Gatorade bottle back and forth until I accidentally kicked it on top of the roof.

Finally, at about 6:30 am my mom was all partied out. As we swerved back home she gloated the whole way how happy she was I was being fucked (yes she really did say that) by such a nice, cute guy. When we got back she told us how she almost scored with a hot guy until some bitch came and screamed at her and ruined it. I’m pretty sure she was unknowingly talking about us.

The next day, she had no memory of what happened and didn’t believe a word we told her, and laughed it off as some prank. Me and M dated for a whole year after that until long distance became too stressful, and we separated. We’ve joked around about it since then (up until I forgot about it) and now he’s back in Texas and we are the best of friends. Oh, and he’s  gay now.

MVWD was dreadful, mostly because it wasn’t even meant as a date.  I was enjoying being single after leaving a really damaging and abusive relationship a month earlier, and had made some new friends while enjoying my newfound freedom. Two guys I met, E and G, lived together with some mutual friends. G and I really hit it off, exchanged numbers and chatted, but he was going home for the winter holidays soon.  E took this chance to regale me with tales of his depressed mother, terrible self-esteem issues, fabulous World of Warcraft victories and totally unrelated (to him) string of academic failures at university.  As this was just before Christmas (and I was clearly the most naive lass in the room), I figured he needed a mate to talk to and invited him and two other people over for a film and dinner.

It turned out to be just the two of us as the others bailed, but I didn’t think anything of it.  E turned up on time with a clinking carrier bag, which seemed odd as the plan was clearly for one film and dinner, and he’d brought enough alcohol for a full-on rave.  Things took a decided downturn when he pulled out a huge bottle of Baileys and a Minnie Mouse doll, which he called Dot and played with (or caressed) all evening.  He’s 23 at this point.  Then, one film turned into all the Disney films in the flat in a row, complete with him singing along to all the music.  My other flatmates were out for the evening, so I couldn’t even conscript them into rescuing me.

After a couple of hours, he’d drunk enough to floor most people and clearly thought he’d scored – based on what I’ve no idea.  He started listing the cheesiest lines of the movies in between howling tunelessly along with The Little Mermaid – complete with the yawn and stretch to put his arm round me.  It felt like he’d learned everything about dating from 1980s teen movies.  I curled up in the corner of the sofa with my arms round my knees, hardly sending out inviting vibes while he trotted out cliche after cliche. We carried on with this ridiculous scenario until about midnight.  Finally, one flatmate returned and I seized the opportunity to turn E out, claiming tiredness and a busy day the next day.

Trying to avoid any sort of awkward goodbye hugging, I showed him out and returned to my room, only to find he’d followed me back without saying a word and was now standing  behind me breathing halitosis on my neck at the (closed) door to my room, waiting expectantly for me to usher him graciously in.

Luckily, before I could freak out properly, my flatmate appeared and kicked E out, having watched him follow me back down the corridor, and we had a good laugh over it.  E’s apparently been doing the same pity-’date’ routine for years, and recently had his crowning moment when he traveled to Sweden to meet a girl he’d befriended on WoW, only to be sent home again within 3 days because she couldn’t take the narcissistic droning and personal space invasions any more.  G and I were engaged three months later, and we’re getting married next year, so this should remain MVWD ever.

MVWD just happened the other day and I didn’t even know it was a date!

An old friend from high school, Bob, recently returned to the US after living abroad for a year or so.  Since his return, we haven’t really spoken or hung out.  I know we both have our own busy lives and I’m perfectly fine doing with an occasional checkup.  Also, it can sometimes get a little awkward with Bob since he is best friends with my ex, Dick.

The other night while I was at a friend’s graduation party, Bob called me up and wanted to chat.  We talked about nothing for a bit and ended up agreeing to meet the next week for lunch and to catch up.  The very next day, Bob texted me to get the when and where for dinner.  I was slightly put off as I thought it was a lunch, but it was just Bob so I thought nothing of it.  We decided on a Thai restaurant near his place since he currently does not have a car and I would need to pick him up.

The day of the dinner arrived and I picked Bob up at the pre-determined time.  The first thing he said upon getting in my car was, “Wow look at that ring!” and wanted to know why I didn’t tell him I was engaged.  I explained that I am planning on getting married but it won’t be for about two years as we are both saving up money for the wedding, honeymoon, a car, and a house.  My fiancé currently lives about two hours away for work and sometimes that two years seems like forever.  The ring belonged to his grandmother and I feel really honored to have gotten it instead of his older brother’s fiancée.  Bob only seemed to half listen and then started talking about cars.

We arrived at the restaurant and within five minutes of sitting down I wanted to leave.  Every conversation I tried to start somehow got turned to sex.  How many girls he has been with, how good he is, how do I deal with having my fiancé so far away, blah, blah, blah.  The poor waitress could see my face and was getting the food out quickly to try and let me leave.  Mercifully, there was almost no conversation as we ate.  We were sitting there waiting for the check when Bob reached across the table and grabbed my hand.  He then proceeded to suggest I come inside back at his place to get intimate since I am most likely really deprived because of my situation; he won’t tell anyone. I forcefully pulled my hand away and said “No way in hell!”

Bob got up and slumped off to the bathroom, most likely to devise a new tactic.  He left his cell phone behind.  I reached across, found my name in his contacts (oh the joys of having a name that starts with A so I can find it quickly) and deleted it.  I threw $40 on the table to cover the food and then ran out to my car and left.  I have no idea how Bob got home.

I met Danielo in Rome, Italy. I was there by myself and he manned the nearest internet cafe to my hotel, so I ended up seeing him daily. We chatted and asked about each other’s families. He was an immigrant from Romania and I was a middle-aged American tourist – we just spent time talking to each other and flirting. Then I flew home and that was that.

Fast forward three years and I’m in Rome again, this time with my daughter. We were sitting on the grass outside the Colisseum and who did I see stroll by but Danielo! I said “hi” and he actually remembered me. We sat on the grass with my daughter chatting and catching up – both so glad we ran into each other again, thinking what were the odds of that! We swapped email addresses and promised to keep in touch this time.

When I was back in the States we e-mailed each other weekly, talking about our jobs and families and just shooting the breeze. His English was only fair so there were times I read his emails and wondered “what the hell was that supposed to mean?” But we had fun anyway and worked hard to keep in touch. I kept inviting him here, he kept inviting me there- it was getting kind of romantic online but I made it very clear I was not his way to marry into American citizenship but I was up for romance. Eventually I planned a trip to Rome to see him.

In his emails he sent me hugs and kisses, told me how much he couldn’t wait to see me, couldn’t wait to hold me- how he was going to take me everywhere and show me everything. I sent him pictures to remind him I wasn’t some hot blonde 20-year-old, but I felt fairly confident because there were plenty of sparks between us the two other times I saw him in Italy and he had seen me in person, after all. After clearing it with him I planned to stay in his apartment while he took an entire week off work. I’d spend a glorious, potentially super romantic foreign romance with a really hot guy.

He picked me up at the airport and reality set it. I have no idea how he could not remember that I wasn’t a skinny, big-boobed American model- he’d seen me in person several times AND had pictures. Realistic, current pictures.

He was rude, obnoxious, and a total jerk. He called everyone around him idiots – often within earshot – and had nothing good to say about anyone, not even his purported friends. The first few days there he dragged me around to run errands (driving like a maniac all the way) and to meet his non-English speaking friends. Then he went back to work and left me on his own in his little, un-airconditioned apartment in the middle of August in Rome. He kept having to work all hours and just blew me off- I was so angry because I’d told him flat out if he was going to be working, I was not going to visit.

On the third day there I booked a room in a hotel and spent most the rest of the trip on my own. Once or twice Danielo arranged to meet me for dinner, but then took off and had nothing else to do with me. I begged him to drive me to the airport the day I had to leave, and he promised me he’d be in front of my hotel first thing in the morning. Of course he blew me off. I felt awful. It was the most humiliating “date” of my life – he clearly had no romantic interest in me once he saw me in person at the airport – and instead of sucking it up and just hanging out as buddies – which I would gladly have done- he totally ditched me.

When I got back home, he had the nerve to act like nothing happened and that I was all angry just because he had to work. He never got it and I stopped talking to him entirely.

One really sweet thing happened on this trip. I was out at dinner one night, entirely alone at a very crowded restaurant in Rome. The maitre’d asked how many and when I said I was solo he loudly exclaimed how could I be alone? He spent the rest of the night paying attention to me. He walked me to my table with my hand on his arm, seated me and asked my name and where I was from. He would call my name across the crowded room just to get my attention and smile at me. He gave me a red rose, bought me an after dinner drink and asked what I was doing after dinner. All the other patrons looked at me like I must be someone special. I will never forget that sweet, sweet waiter, no matter how long I live.

I met a guy on a dating site, but he worked the graveyard shift at an apartment complex, so we had an early morning date. I’ve only been an adult for a few months, so my parents who I lived with were nervous I might add. Plus, I only had talked to him for a few hours, but I had a good feeling. He texted me to call him because he was a bit lost onto my house, so I was giving him directions when all of a sudden I hear a slight noise and him saying “Oh, shit..I crashed..”

I started laughing and said that’s not funny. Then I stopped when I heard sirens. Thankfully, he was fine, and so was his amazing vintage car. So he picked me up and we went bowling, arcade, and a movie. We went back to his place to watch Dawn of the Dead and we both fell asleep. Unfortunately I did not hear my phone, with the 12 texts and 5 voicemails from my Mother, Father, Brother, AND Best Friend. I did however wake up to him shaking me awake saying there was a police officer on the phone.

The best part of the date? He met my parents and said he couldn’t wait for a second date. I think he’s a keeper.

MVWD happened a few years ago, when I waitressed at a strip club. I met a man online, after having a few successful dates through the service. He picked me up and we went to dinner at a nice restaurant. Within five minutes of sitting down, he loudly began talking about how fat the girl near us was. I was a bit offended, because she couldn’t have weighed more than 10 lbs more than me, but I decided to ignore him and continue the date. Then he insulted a gay man he knew, saying how unnatural it is. I informed him that my uncle and several of my friends are gay, and he dropped it. Before our dinner came, he insulted interracial couples and biracial people. While I am not biracial, my sister and brother are, and I told him so. Then he proceeded to insult women who have kids by more than one person, and I informed him that obviously my mother had more than one father, and asked if that made him a whore in his mind. He said, “If the shoe fits.” He attempted to try and convince me to go home with him, and I told him no.

About a week later, I got an email from him asking me to please set him up with one of my stripper friends, at which point I informed him that I wouldn’t wish him on my worst enemy, unless my worst enemy was an overweight biracial homosexual with kids by several different people. I never heard from him again. I did get lucky some time later with internet dating, and have been with my fiance for 4 years now, after meeting him in a chat room, but that date almost ruined the internet for me.